Dress pants
#41
The dollar stores (everything a buck) has velcro straps that are made for a multitude of uses. Several in a pack. About an inch wide and long enough to go around your ankle. They come in several neutral colors. Cut them to fit your ankle. Can't beat it for $1. You can also get fancier versions at the office supply stores for a couple of dollars more.
#42
I am in the same boat, I wear a pair of carhartt double dungarees over my dress pants and simply take them off when I get to work. I always buy a pair at least one size larger than I normally wear to make putting them on over the dress pants I am wearing. It's hot is MS in the summer but they don't seem to add to the heat unless I am stopped in traffic.
#44
I rarely say things look gay, but I have tried that, and I quickly stopped it. Because it looked gay.
#45
Got to a bicycle shop and get he Velcro straps or get the rubber straps with the clip at both ends to go under the boots, they have them in most bike shops.
#48
when i ride to work, i tend to hug the air cleaner/tank area with my knees a bit and it keeps the pants from blowing up. not sure why it makes such a difference, but it does. dyna with forwards. also found that if i wear my riding boots that the pants tend to "stick" to them better and don't ride up.